2-halo-N-(azole-1-yl-methyl)-substituted acetanilides

ABSTRACT

New and valuable 2-halo-N-(azole-1-yl-methyl)-substituted acetanilides and having a good herbicidal action, and methods of controlling the growth of unwanted plants with these compounds.

The present invention relates to new and valuable acetanilides, methods of manufacturing them, herbicides containing these compounds, and methods of controlling the growth of unwanted plants with these compounds.

Haloacetanilides having herbicidal or growth-regulating properties are known from the literature. Of particular importance are active ingredients such as 2-chloro-N-isopropylacetanilide (German No. 1,014,380) and 2-chloro-2',6'-diethyl-N-methoxymethyl-acetanilide (U.S. Pat. No. 3,547,620). Furthermore, haloacetanilides with heterocyclic substituents have been disclosed, e.g., compounds bearing a 1,3-dioxolan-2-ylmethyl group on the nitrogen atom (German Laid-Open Application DOS No. 2,405,510). In the examples in these publications illustrating activity, it is apparent that the action of the compounds mentioned therein is restricted to a few grassy species generally easily combatted with haloacetanilides. Moreover, the relatively high dosage rates employed for some of these prior art compounds are indicative of low activity.

We have found that acetanilides of the formula ##STR1## where R denotes hydrogen, alkyl of a maximum of 5 carbon atoms, or alkoxy of a maximum of 5 carbon atoms, R¹ denotes hydrogen, halogen, alkyl of a maximum of 5 carbon atoms, alkoxy of a maximum of 5 carbon atoms, perhaloalkyl of a maximum of 4 carbon atoms, or 1-alkoxyalkyl of a maximum of 5 carbon atoms, R² denotes hydrogen, halogen, alkyl of a maximum of 5 carbon atoms, alkoxy of a maximum of 5 carbon atoms, perhaloalkyl of a maximum of 4 carbon atoms, or alkoxyalkyl of a maximum of 5 carbon atoms, or forms, together with R, an alkylene chain of a maximum of 6 carbon atoms which is attached in the orthoposition and is optionally substituted by alkyl of a maximum of 4 carbon atoms, X denotes chloro, bromo, or iodo, and A denotes azole which is linked via a ring nitrogen atom and is unsubstituted or mono- or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl, each of a maximum of 4 carbon atoms, cyano, carboxy, carbalkoxy of a maximum of 4 carbon atoms in the alkoxy group, or alkanoyl of a maximum of 4 carbon atoms, A also being able to denote salts of azoles containing 2 or 3 nitrogen atoms, have a surprisingly strong and selective herbicidal action.

In view of the state of the art, it was surprising that the heterocyclic substituted acetanilides according to the invention exhibit such an excellent and intense action on a broad spectrum of unwanted plants. Depending on the objective, the new active ingredients are suitable for the total removal of plant growth, for the selective elimination of unwanted plants from specific herbaceous or woody crop plants, or for growth regulation by inhibition.

Particularly marked selectivity between weeds and crop plants is exhibited even at low application rates by compounds of the invention according to the formula I in which R and R¹ are substituents in the 2- and 6-positions on the phenyl nucleus and each denotes alkyl of a maximum of 5 carbon atoms.

Suitable meanings for R, R¹, R², X and A in formula I are as follows:

R: hydrogen, alkyl of a maximum of 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, linear and branched pentyl, alkoxy of a maximum of 5 carbon atoms such as methoxy, ethoxy, propoxy, butoxy and pentyloxy;

R¹ : hydrogen, halogen, alkyl of a maximum of 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, linear and branched pentyl, alkoxy of a maximum of 5 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, perhaloalkyl of a maximum of 4 carbon atoms, such as trifluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, alkoxyalkyl of a maximum of 5 carbon atoms, such as methoxymethyl and ethoxyethyl;

R² : hydrogen, halogen, alkyl of a maximum of 5 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, linear and branched pentyl, alkoxy of a maximum of 5 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, perhaloalkyl of a maximum of 4 carbon atoms, such as trifluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, alkoxyalkyl of a maximum of 5 carbon atoms, such as methoxymethyl and ethoxymethyl;

R² together with R: an alkylene chain of a maximum of 6 carbon atoms which is attached in the ortho-position and is optionally substituted by alkyl of a maximum of 4 carbon atoms, such as ethylene, trimethylene, tetramethylene, 1-methyltrimethylene, 1,1-dimethyltrimethylene, 1,1-dimethyltetramethylene;

X: chlorine, bromine, and iodine, preferably chlorine;

A: azole linked by a ring nitrogen atom, such as pyrrole, pyrazole, 1,2,4-triazole, 1,2,3-triazole, or tetrazole, which is unsubstituted or mono- or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl, each of a maximum of 4 carbon atoms, cyano, carboxy, carbalkoxy with a maximum of 4 carbon atoms in the alkoxy group, or alkanoyl of a maximum of 4 carbon atoms, the substituents being identical or different, e.g., 2,6-dimethylpyrrole, tetramethylpyrrole, 3(5)-methylpyrazole, 4-methylpyrazole, 3(5)-ethylpyrazole, 4-ethylpyrazole, 3(5)-isopropylpyrazole, 4-isopropylpyrazole, 3,5-dimethylpyrazole, 3,5-dimethyl-4-acetylpyrazole, 3,5-dimethyl-4-propionylpyrazole, 3,4,5-trimethylpyrazole, 3(5)-phenylpyrazole, 4-phenylpyrazole, 3,5-diphenylpyrazole, 3(5)-phenyl-5(3)-methylpyrazole, 3(5)-chloropyrazole, 4-chloropyrazole, 4-bromopyrazole, 4-iodopyrazole, 3,4,5-trichloropyrazole, 3,4,5-tribromopyrazole, 3,5-dimethyl-4-chloropyrazole, 3,5-dimethyl-4-bromopyrazole, 4-chloro-3(5)-methylpyrazole, 4-bromo-3(5)-methylpyrazole, 4-methyl-3,5-dichloropyrazole, 3(5)-methyl-4,5( 3)-dichloropyrazole, 3(5)-chloro-5(3)-methylpyrazole, 4-methoxypyrazole, 3(5)-methyl-5(3)-methoxypyrazole, 3(5)-ethoxy-4,5(3)-dimethylpyrazole, 3(5)-methyl-5(3)-trifluoromethylpyrazole, 3,5-bis-trifluoromethylpyrazole, 3(5)-methyl-5(3)-carbethoxypyrazole, 3,5-bis-carboethoxypyrazole, 3,4,5-triscarbethoxypyrazole, 3(5)-methyl-5(3)-methylthio-4-carbethoxypyrazole, 4-methyl-3,5-bis-carbethoxypyrazole, 4-cyanopyrazole, 4-methoxy-3,5-dichloropyrazole, 3(5)-methyl-1,2,4-triazole, 3,5-dimethyl-1,2,4-triazole, 3(5)-chloro-1,2,4-triazole, 3(5)-bromo-1,2,4-triazole, 3(5)-chloro-5(3)-methyl-1,2,4-triazole, 3,5-dichloro-1,2,4-triazole, 3,5-dibromo-1,2,4-triazole, 3(5)-chloro-5(3)-cyano-1,2,4-triazole, 3(5)-chloro-5(3)-phenyl-1,2,4-triazole, 3(5)-chloro-5(3)-carbomethoxy-1,2,4-triazole, 3(5)-methylthio-1,2,4-triazole, 4(5)-methyl-1,2,3-triazole, 4,5-dimethyl-1,2,3-triazole, 4(5)-phenyl-1,2,3-triazole, 4(5)-chloro-1,2,3-triazole, 1,2,3-triazol-4(5)-yl carboxylic acid ethyl ester, 1,2,3-triazol-4,5-yl dicarboxylic acid dimethyl ester, 5-methyltetrazole, 5-chlorotetrazole, tetrazolyl-5-carboxylic acid ethyl ester, imidazole, 2-methylimidazole, 4,5-dichloroimidazole, 2-methyl-4,5-dichloroimidazole, 2-ethyl-4,5-dichloroimidazole, 2-isopropyl-4,5-dichloroimidazole, 2,4,5-trichloroimidazole, 2,4,5-tribromoimidazole, and 2-bromo-4,5-dichloroimidazole.

Furthermore, the radical A, when the optionally substituted azole contains 2 or 3 nitrogen atoms, may be bound to one of the usual strong inorganic or organic acids, e.g., hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, tetrafluoboric acid, fluosulfonic acid, and formic acid, a halogenated carboxylic acid, e.g., trichloroacetic acid, an alkanesulfonic acid, e.g., methanesulfonic acid, a halogenated alkanesulfonic acid, e.g., trifluoromethanesulfonic acid and perfluorohexanesulfonic acid, or an arylsulfonic acid, e.g., dodecylbenzenesulfonic acid, to give a salt.

With certain asymmetrically substituted azoles, e.g., pyrazole, 1,2,3-triazole and 1,2,4-triazole, two isomers appear because of tautomeric structures in the starting materials; pyrazole is given here by way of example: ##STR2##

In these instances, two isomers appear in the compounds of the formula I; their ratio to each other is essentially determined by the kind of radicals B, C and D, and may be of importance for the herbicidal properties.

The new acetanilides of the formula I may be prepared by the following processes.

The acetanilides of the formula I are obtained by reaction of 2-halo-N-halomethyl acetanilides of the formula II with a 1H azole of the formula H-A in accordance with the equation ##STR3##

The substituents R, R¹, R² and X have the above meanings and A denotes azole attached via a ring nitrogen atom and which is unsubstituted or mono- or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl, each of a maximum of 4 carbon atoms, cyano, carboxy, carbalkoxy with a maximum of 4 carbon atoms in the alkoxy group, or alkanoyl with a maximum of 4 carbon atoms.

Some of the 2-halo-N-halomethyl acetanilides of the formula II are known from German Published Application DAS No. 1,542,950; others may be prepared analogously by reaction of the appropriate azomethines with a haloacetyl halide.

The 1H azole is expediently employed in at least a molar amount, with reference to 2-halo-N-halomethyl acetanilide.

The hydrogen halide liberated during the reaction is advantageously intercepted by suitable binding agents such as organic bases, e.g., tertiary amines, or organic bases, e.g., alkali metal or alkaline earth metal carbonates or bicarbonates. The hydrogen halide binder is added in an at least molar amount, with reference to 1H azole employed.

It is advantageous to carry out the reaction in a solvent inert to 2-halo-N-halomethyl acetanilides. Suitable solvents are hydrocarbons, e.g., petroleum ether, ligroin, cyclohexane, toluene and xylene; ethers, e.g., diethyl ether, diisopropyl ether, dimethoxyethane, tetrahydrofuran, dioxane, and anisole; halogenated hydrocarbons, e.g., dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride, and chlorobenzene; ketones, e.g., acetone, and methyl ethyl ketone; esters, e.g., ethyl acetate, and butyl acetate; and sulfones, e.g., dimethyl sulfoxide, and tetrahydrothiophene-1,1-dioxide. Mixtures of these solvents may also be used.

The reaction may be carried out at temperatures of from 0° C. upwards. To accelerate the reaction, it is advantageous to carry it out at the boiling point of the solvent or solvent mixture, but not above 200° C. Preferred temperatures are from 50° to 150° C. Upon completion of the reaction the mixture is subjected to filtration and the product is, if desired after washing, isolated from the filtrate in conventional manner. If a solvent miscible with water is used, it is usually advantageous to remove it, after filtration, by evaporation and to replace it by a solvent immiscible with water.

The new acetanilides of the formula I may also be prepared by reaction of 2-halo-N-halomethyl acetanilides of the formula II with a salt of an azole of the formula M.sup.⊕ A.sup.⊖, in accordance with the following equation: ##STR4##

The substituents R, R¹, R² and X have the above meanings, M.sup.⊕ denotes a silver ion, an alkali metal ion or an equivalent of an alkaline earth metal ion, and A denotes azole attached via a ring nitrogen atom and which is unsubstituted or mono- or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl, each of a maximum of 4 carbon atoms, cyano, carboxy, carbalkoxy of a maximum of 4 carbon atoms in the alkoxy group, or alkanoyl of a maximum of 4 carbon atoms.

The alkali metal, alkaline earth metal or silver azoles M.sup.⊕ A.sup.⊖ are prepared in known manner by reaction of the 1H azole H-A with alkali metals or strong bases, e.g., alkali metal hydroxide, alkali metal alcoholate, alkali metal amide, alkali metal hydride, and silver hydroxide, with the liberation of hydrogen, alcohol or ammonia.

The reaction of the salts of M.sup.⊕ A.sup.⊖ with the 2-halo-N-halomethyl acetanilides of the formula II is advantageously carried out in polar aprotic solvents such as nitriles, e.g,, acetonitrile, amides, e.g., dimethylformamide, polyethers, e.g., diethylene glycol dimethyl ether and triethylene glycol dimethyl ether, sulfones, e.g., tetrahydrothiophene-1,1-dioxide, sulfoxides, e.g., dimethyl sulfoxide, and ketones, e.g., acetone, methyl ethyl ketone and diisopropyl ketone, at temperatures of from -30° to +50° C., preferably at room temperature. The starting materials are expediently employed in equimolar amounts. The reaction products are--if desired, after separation of the inorganic salts M.sup.⊕ A.sup.⊖ formed and if desired after replacement of the polar aprotic solvent by a solvent immiscible with water--isolated in conventional manner.

Acetanilides of the formula I ##STR5## where R, R¹, R² and X have the above meanings and A denotes azole (with 2 or 3 nitrogen atoms in the ring) attached via a ring nitrogen atom and unsubstituted or mono- or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl, each of a maximum of 4 carbon atoms, cyano, carboxy, carbalkoxy of a maximum of 4 carbon atoms in the alkoxy group, or alkanoyl of a maximum of 4 carbon atoms, may be prepared by reaction of substituted anilines of the formula III with a hydrohalide, preferably hydrochloride, of a halomethyl azole of the formula X--CH₂ --A to give a secondary aniline of the formula IV, and by further reaction of this secondary aniline with a haloacetyl halide of the formula X--CO--CH₂ --X in accordance with the equation ##STR6##

As halomethyl azoles, chloromethyl azoles are preferred. Chloromethylpyrazole hydrochloride and its manufacture are disclosed in J. Chem. Soc., 1960, 5272-3. Other chloromethyl azoles may be prepared analogously.

With asymmetrically substituted chloromethyl azoles in which the azole is a pyrazole, a 1,2,3-triazole or a 1,2,4-triazole,two isomers also appear because of tautomeric structures.

Both process steps require the presence of an agent which binds hydrogen halide; suitable compounds for the first stage are tertiary organic amines such as triethylamine, ethyl diisopropylamine, diazabicyclo-[2,2,2]-octane, diethylcyclohexylamine, pyridine, and alkylpyridine, and organic bases such as alkali metal or alkaline earth metal carbonates or bicarbonates, or substituted anilines of the formula III; suitable compounds for the second stage are only the first mentioned bases and not the substituted anilines.

Both reactions are advantageously carried out in a polar aprotic solvent such as nitriles, e.g., acetonitrile, amides, e.g., dimethylformamide, polyethers, e.g., diethylene glycol dimethyl ether, and triethylene glycol dimethyl ether, sulfones, e.g., tetrahydrothiophene-1,1-dioxide, sulfoxides, e.g., dimethyl sulfoxide, and ketones, e.g. acetone, methyl ethyl ketone, and diisopropyl ketone.

The reaction to give the secondary aniline of the formula IV takes place in the temperature range of from 20° to 150° C.; the further reaction with the haloacetyl halide in the range of from -20° to +100° C.

The starting materials are advantageously employed in equimolar amounts. The secondary aniline of the formula IV may, if desired, be further reacted with haloacetyl halides without being isolated.

Acetanilides of the formula I ##STR7## where R, R¹, R² and X have the above meanings and A denotes a 1,2,3-triazole attached via a ring nitrogen atom and unsubstituted or mono- or polysubstituted by phenyl, alkyl of a maximum of 4 carbon atoms, carboxy, or carbalkoxy with a maximum of 4 carbon atoms in the alkoxy group, may also be obtained by reaction of 2-halo-N-halomethyl acetanilides of the formula II with an alkali metal azide and further reaction of the 2-halo-N-azidomethyl acetanilide of the formula V, thus obtained, with acetylene, the hydrogen atoms of which may be replaced by the groups given as substituents for the triazolyl radical, in accordance with the following equation: ##STR8## R, R¹, R² and X have the above meanings, M.sup.⊕ denotes an alkali metal ion, R³ and R⁴ are identical or different and each denotes hydrogen, phenyl, alkyl of a maximum of 4 carbon atoms, carboxy, carbalkoxy of a maximum of 4 carbon atoms in the alkoxy group, or alkanoyl of a maximum of 4 carbon atoms.

The 2-halo-N-halomethyl acetanilides of the formula II are reacted with at least molar amounts of an alkali metal azide, preferably sodium azide, in an aprotic polar solvent at temperatures of from -30° to +50° C., preferably room temperature.

Particularly suitable aprotic polar solvents are tertiary amides such as dimethylformamide and N,N-dimethylacetamide, nitriles such as acetonitrile, and sulfones such as tetrahydrothiophene-1,1-dioxide and dimethyl sulfoxide.

The 2-halo-N-azidomethyl acetanilide of the formula V is expediently reacted as crude product with at least molar amounts of acetylene or an acetylene derivative in a solvent inert to the reactants to give a 2-halo-N-(1,2,3-triazol-1-yl-methyl)-acetanilide. It is advantageous to remove, before the reaction, the alkali metal azide still present by washing with water.

The reaction with acetylene or an acetylene derivative may, depending on the reactivity of the reactants, be carried out at from 0° to 150° C. and at atmospheric or superatmospheric pressure. Suitable solvents inert to the reactants are aprotic nonpolar solvents such as chlorinated aliphatic and aromatic hydrocarbons, e.g., dichloromethane, carbon tetrachloride, 1,2-dichloroethane and chlorobenzenes, and ethers such as diethyl ether, dioxane, tetrahydrofuran and anisole.

The salts of the acetanilides of the formula I, A denoting an azole with 2 or 3 nitrogen atoms, preferably pyrazole, 1,2,3-triazole and 1,2,4-triazole, may be obtained in conventional manner from the acetanilides of the formula I, which may be prepared by one of the processes described above, by adding at least a molar amount of a strong inorganic or organic acid, e.g., hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, tetrafluoboric acid, fluosulfonic acid and formic acid, a halogenated carboxylic acid, e.g., trichloroacetic acid, an alkanesulfonic acid, e.g., methanesulfonic acid, a halogenated alkanesulfonic acid, e.g., trifluoromethanesulfonic acid and perfluorohexanesulfonic acid, or an arylsulfonic acid, e.g., dodecylbenzenesulfonic acid.

The preparation of the new acetanilides and salts thereof is illustrated by the following examples, in which parts by weight bear the same relationship to parts by volume as kilograms to liters.

EXAMPLE 1

16.5 parts by weight of 2-chloro-2',6'-dimethyl-N-chloromethyl acetanilide and 9.3 parts by weight of 1,2,4-triazole are refluxed for 8 hours in 60 parts by volume of anhydrous tetrahydrofuran. After the mixture has been cooled, it is filtered, the filtrate is concentrated in vacuo, and the residue is dissolved in 60 parts by volume of chloroform, washed 3 times with water, each time with 40 parts by volume, and dried over sodium sulfate. After evaporation of the solvent in vacuo, there is isolated 21.0 parts by weight of 2-chloro-2',6'-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide, m.p.: 115°-118° C.; after recrystallization from ethanol, it melts at 120° C.

    ______________________________________                                         C.sub.13 H.sub.15 ClN.sub.4 O (molecular weight: 279)                                  C           H     N                                                    ______________________________________                                         calc.:    56.0          5.4   20.1                                             found:    56.2          5.6   19.7                                             ______________________________________                                    

EXAMPLE 2

43.9 parts by weight of 2-chloro-2',6'-dimethyl-N-chloromethyl acetanilide and 25.8 parts by weight of pyrazole are stirred for 7 hours at 90° C. in 120 parts by volume of toluene. After the mixture has cooled it is filtered, and the filtrate is washed 3 times with water, each time with 50 parts by volume, and dried over sodium sulfate. The solvent is evaporated and the residue pasted with 50 parts by volume of petroleum ether to give 39.1 parts by weight of 2-chloro-2',6'-dimethyl-N-(pyrazol-1-yl-methyl)-acetanilide, m.p.: 81° C.

    ______________________________________                                         C.sub.14 H.sub.16 ClN.sub.3 O (molecular weight: 278)                                  C           H     N                                                    ______________________________________                                         calc.:    60.5          5.8   15.1                                             found:    60.7          5.8   14.7                                             ______________________________________                                    

EXAMPLE 3

68.5 parts by weight of 2-chloro-2',6'-diethyl-N-chloromethyl acetanilide and 50.4 parts by weight of 3,5-dimethylpyrazole are stirred in 100 parts by volume of toluene for 8 hours at from 90° to 95° C. After the mixture has cooled to room temperature, it is filtered, and the filtrate is washed 3 times with water, each time with 100 parts by volume, and dried over sodium sulfate. After evaporation of the solvent in vacuo, 42.5 parts by weight of 2-chloro-2',6'-diethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)-acetanilide (m.p. 107°-109° C.) is isolated by pasting the residue with 70 parts by volume of petroleum ether.

    ______________________________________                                         C.sub.18 H.sub.24 ClN.sub.3 O (molecular weight: 334)                                  C           H     N                                                    ______________________________________                                         calc.:    64.8          7.2   12.6                                             found:    64.6          7.2   12.5                                             ______________________________________                                    

EXAMPLE 4

21.4 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-chloromethyl acetanilide and 20.2 parts by weight of 4-chloro-3,5-dimethylpyrazole are refluxed for 10 hours in 100 parts by volume of glycol dimethyl ether. After cooling the mixture to 0° C., it is filtered, and the filtrate, concentrated to 23.8 parts by weight, is filtered with 600 parts by volume of chloroform through 50 parts by weight of silica gel. From the concentrated chloroform filtrate there is isolated 20.4 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-(4-chloro-3,5-dimethylpyrazol-1-yl-methyl)-acetanilide as an oil which completely crystallizes upon milling with 50 ml of petroleum ether (m.p. 66° C. from petroleum ether).

    ______________________________________                                         C.sub.17 H.sub.21 Cl.sub.2 N.sub.3 O (molecular weight: 354)                           C           H     N                                                    ______________________________________                                         calc.:    57.6          6.0   11.9                                             found:    57.8          6.0   11.5                                             ______________________________________                                    

EXAMPLE 5

28.5 parts by weight of 2-chloro-N-chloromethyl-2'-methyl-6'-ethyl acetanilide and 17.4 parts by weight of 3(5)-methyl-1,2,4-triazole are refluxed for 6 hours in 150 parts by volume of anhydrous tetrahydrofuran. After the mixture has cooled to 0° C., it is filtered, the filtrate is concentrated in vacuo, and the residue is thoroughly milled with 200 parts by volume of water, suction filtered and dried. There is obtained 20.5 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-(3(5)-methyl-1,2,4-triazol-1-yl-methyl)-acetanilide as a crystalline powder (m.p. 89°-91° C.), which melts at 90° to 93° C. after recrystallization from a 3:1 mixture of toluene and petroleum ether; the 3(5)-position isomer ratio is 3:1.

    ______________________________________                                         C.sub.15 H.sub.19 ClN.sub.4 O (molecular weight: 306.5)                                C           H     N                                                    ______________________________________                                         calc.:    58.7          6.2   18.3                                             found:    58.8          6.3   17.9                                             ______________________________________                                    

EXAMPLE 6

3.5 parts by weight of 1,2,4-triazole is dissolved in 8.8 parts by weight of 30% strength sodium methylate solution; the resulting solution is evaporated to dryness in vacuo at 50° C. This crystalline residue is introduced in portions into a solution of 13.0 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-chloromethyl acetanilide in 80 parts by volume of anhydrous acetonitrile, while stirring and at room temperature. After 24 hours the undissolved matter is filtered off and the filtrate is concentrated in vacuo. The residue is filtered with 300 parts by volume of chloroform through 60 parts by weight of silica gel to give, after evaporation of the eluate, 8.0 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide; m.p.: 84° C.

    ______________________________________                                         C.sub.14 H.sub.17 ClN.sub.4 O (molecular weight: 293)                                  C           H     N                                                    ______________________________________                                         calc.:    57.4          5.9   19.1                                             found:    57.9          6.0   18.6                                             ______________________________________                                    

EXAMPLE 7

At 25° to 30° C. 6.5 parts of sodium azide is introduced in portions into a solution of 26.1 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-chloromethyl acetanilide in 100 parts of anhydrous dimethylformamide, and the whole is stirred for 2 hours. After the addition of 200 parts by volume of water, the organic phase is separated, taken up in 200 parts by volume of methylene chloride, washed 3 times with water, each time with 50 parts by volume, and dried over sodium sulfate. After filtration, 14.2 parts by volume of the dimethyl ester of acetylenedicarboxylic acid is dripped in, the temperature rising to 30° C. After 2 hours, the mixture is concentrated in vacuo. From the residue there is obtained, after milling with methanol, 21.5 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-(4,5-bis-carbomethoxy-1,2,3-triazol-1-yl-methyl)-acetanilide; m.p.: 103°-105° C.

EXAMPLE 8

10.0 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide is dissolved in 50 parts by volume of a mixture of anhydrous dichloromethane and ether (1:1). Dry hydrogen chloride is then passed in, while cooling, for 15 minutes, and a further 55 parts by volume of anhydrous ether is dripped in. The precipitated crystals are suction filtered, and there is obtained 7.5 parts by weight of 2-chloro-2'-methyl-6'-ethyl-N-(1,2,4-triazol-1-yl-methyl)acetanilide hydrochloride; m.p.: 148° C.

    ______________________________________                                         C.sub.14 H.sub.18 Cl.sub.2 N.sub.4 O (molecular weight: 329)                           C           H     N                                                    ______________________________________                                         calc.:    51.1          5.5   17.0                                             found:    51.4          5.6   17.0                                             ______________________________________                                    

The following compounds are obtained analogously:

    __________________________________________________________________________      ##STR9##                                                                      No. R      R.sup.1                                                                               R.sup.2                                                                             X A                   m.p. (°C.)                 __________________________________________________________________________     1   H      H      H    Cl                                                                                ##STR10##          98                                2   2-CH.sub.3                                                                            H      H    Cl                                                                               "                   oil                               3   2-C.sub.2 H.sub.5                                                                     H      H    Cl                                                                               "                   oil                               4   2-CH(CH.sub.3).sub.2                                                                  H      H    Cl                                                                               "                   54                                5   2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                               "                   81                                6   2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Br                                                                               "                                                     7   2-C.sub.2 H.sub.5                                                                     6-CH.sub.3                                                                            H    Cl                                                                               "                   56                                8   2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   68                                9   6-CH.sub.3                                                                            2-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                   91                                10  6-CH.sub.3                                                                            2-C(CH.sub.3).sub.3                                                                   H    Cl                                                                               "                                                     11  2-CH(CH.sub.3).sub.2                                                                  6-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                   132                               12  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Br                                                                               "                                                     13  2-CH.sub.3                                                                            6-CH.sub.3                                                                            4-CH.sub.3                                                                          Cl                                                                               "                   92                                14  2-CH.sub.3                                                                            6-CH.sub.3                                                                            3-CH.sub.3                                                                          Cl                                                                               "                   84                                15  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     4-CH.sub.3                                                                          Cl                                                                               "                                                     16  5-CH.sub.3                                                                            4-CH.sub.3                                                                            2-CH.sub.3                                                                          Cl                                                                               "                                                     17  H      2-CH.sub.3                                                                            3-CH.sub.3                                                                          Cl                                                                               "                   102                               18  H      2-CH.sub.3                                                                            4-CH.sub.3                                                                          Cl                                                                               "                   oil                               19  H      2-CH.sub.3                                                                            5-CH.sub.3                                                                          Cl                                                                               "                   oil                               20  H      2-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                   100                               21  6-CH.sub.3                                                                            3-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                                                     22  2-CH.sub.3                                                                            3-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                   oil                               23  H      2-CH.sub.3                                                                            4-Cl Cl                                                                               "                                                     24  2-CH.sub.3                                                                            H      5-Cl Cl                                                                               "                   oil                               25  6-Cl   2-CH.sub.3                                                                            H    Cl                                                                               "                                                     26  H      3-Cl   H    Cl                                                                               "                   125                               27  H      3-Cl   5-Cl Cl                                                                               "                   126                               28  6-Cl   2-Cl   H    Cl                                                                               "                                                     29  4-CH.sub.3 O                                                                          3-Cl   2-CH.sub.3                                                                          Cl                                                                               "                                                     30  H      2,3-(CH.sub.2).sub.3                                                                       Cl                                                                               "                                                     31  H      2,3-(CH.sub.2 ).sub.4                                                                      Cl                                                                               "                                                     32  6-CH.sub.3                                                                            2,3-(CH.sub.2).sub.3                                                                       Cl                                                                               "                                                     33  H      3,4-(CH.sub.2).sub.3                                                                       Cl                                                                               "                   oil                               34  H      H      H    Cl                                                                                ##STR11##          90                                35  2-CH.sub.3                                                                            H      H    Cl                                                                               "                   94                                36  2-C.sub.2 H.sub.5                                                                     H      H    Cl                                                                               "                   121                               37  2-CH(CH.sub.3).sub.2                                                                  H      H    Cl                                                                               "                   129                               38  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                               "                   126                               39  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Br                                                                               "                                                     40  2-C.sub.2 H.sub.5                                                                     6-CH.sub.3                                                                            H    Cl                                                                               "                   89-91                             41  2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   107-9                             42  6-CH.sub.3                                                                            2-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                   131                               43  6-CH.sub.3                                                                            2-CH(CH.sub.3).sub.3                                                                  H    Cl                                                                               "                                                     44  2-CH(CH.sub.3).sub.2                                                                  6-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                   128                               45  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Br                                                                               "                                                     46  2-CH.sub.3                                                                            6-CH.sub.3                                                                            4-CH.sub. 3                                                                         Cl                                                                               "                   100                               47  2-CH.sub.3                                                                            6-CH.sub.3                                                                            3-CH.sub.3                                                                          Cl                                                                               "                   98                                48  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     4-CH.sub.3                                                                          Cl                                                                               "                                                     49  5-CH.sub.3                                                                            4-CH.sub.3                                                                            2-CH.sub.3                                                                          Cl                                                                               "                                                     50  H      2-CH.sub.3                                                                            3-CH.sub.3                                                                          Cl                                                                               "                   129                               51  H      2-CH.sub.3                                                                            4-CH.sub.3                                                                          Cl                                                                               "                   viscous mass                      52  H      2-CH.sub.3                                                                            5-CH.sub.3                                                                          Cl                                                                               "                   86                                53  H      2-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                   oil                               54  6-CH.sub.3                                                                            3-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                                                     55  2-CH.sub.3                                                                            3-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                   138                               56  H      2-CH.sub.3                                                                            4-Cl Cl                                                                               "                                                     57  H      2-CH.sub.3                                                                            5-Cl Cl                                                                               "                   138                               58  6-Cl   2-CH.sub.3                                                                            H    Cl                                                                               "                                                     59  H      3-Cl   5-Cl Cl                                                                               "                                                     60  6-Cl   2-Cl   H    Cl                                                                               "                                                     61  4-CH.sub.3 O                                                                          3-Cl   2-CH.sub.3                                                                          Cl                                                                               "                                                     62  H      3-CF.sub.3                                                                            H    Cl                                                                               "                   102                               63  H      2,3-(CH.sub.2).sub.3                                                                       Cl                                                                               "                                                     64  H      2,3-(CH.sub.2).sub.4                                                                       Cl                                                                               "                                                     65  6-CH.sub.3                                                                            2,3-(CH.sub.2).sub.3                                                                       Cl                                                                               "                                                     66  H      3,4-(CH.sub.2 ).sub.3                                                                      Cl                                                                               "                   105                               67  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR12##          63-66                             68  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   oil                               69  2-C.sub.2 H.sub.5                                                                     H      H    Cl                                                                               "                   oil                               70  2-C.sub.2 H.sub.5                                                                     2-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   90-94                             71  2-CH.sub.3                                                                            2-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                                                     72  2-CH(CH.sub.3).sub.2                                                                  H      H    Cl                                                                               "                   oil                               73  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR13##          102                               74  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   72                                75  2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     76  2-CH.sub.3                                                                            6-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                                                     77  H      H      H    Cl                                                                                ##STR14##          114                               78  2-CH.sub.3                                                                            H      H    Cl                                                                               "                   82                                79  2-C.sub.2 H.sub.5                                                                     H      H    Cl                                                                               "                   78                                80  2-CH(CH.sub.3).sub.2                                                                  H      H    Cl                                                                               "                   143                               81  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                               "                   oil                               82  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     83  2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     84  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR15##          143                               85  2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   85                                86  H      H      H    Cl                                                                                ##STR16##          115                               87  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                               "                   150                               88  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   132                               89  2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   99                                90  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR17##                                            91  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   145                               92  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR18##          115                               93  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   125                               94  2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   126                               95  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR19##          104                               96  2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   94                                97  2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   111                               98  2-CH.sub.3                                                                            6-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                                                     99  2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR20##          102                               100 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   80                                101 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   113                               102 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR21##                                            103 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR22##                                            104 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     105 H      H      H    Cl                                                                                ##STR23##          111                               106 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                               "                   105                               107 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   63-66                             108 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   88                                109 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR24##                                            110 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     111 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     112 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR25##                                            113 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR26##          oil                               114 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     115 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR27##                                            116 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR28##          130                               117 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     118 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     119 2-CH.sub.3                                                                            6-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                                                     120 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR29##                                            121 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR30##                                            122 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR31##                                            123 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR32##                                            124 H      H      H    Cl                                                                                ##STR33##          139                               125 2-C.sub.2 H.sub.5                                                                     H      H    Cl                                                                               "                   94                                126 2-CH(CH.sub.3).sub.2                                                                  H      H    Cl                                                                               "                   116                               127 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                               "                   120                               128 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Br                                                                               "                                                     129 2-C.sub.2 H.sub.5                                                                     6-CH.sub.3                                                                            H    Cl                                                                               "                   84                                130 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   114                               131 6-CH.sub.3                                                                            2-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                   128                               132 6-CH.sub.3                                                                            2-C(CH.sub.3).sub.3                                                                   H    Cl                                                                               "                                                     133 2-CH(CH.sub.3).sub.2                                                                  6-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                   126                               134 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Br                                                                               "                                                     135 2-CH.sub.3                                                                            6-CH.sub.3                                                                            4-CH.sub.3                                                                          Cl                                                                               "                   90                                136 2-CH.sub.3                                                                            6-CH.sub.3                                                                            3-CH.sub.3                                                                          Cl                                                                               "                   105                               137 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     4-CH.sub.3                                                                          Cl                                                                               "                                                     138 5-CH.sub.3                                                                            4-CH.sub.3                                                                            2-CH.sub.3                                                                          Cl                                                                               "                                                     139 H      2-CH.sub.3                                                                            3-CH.sub.3                                                                          Cl                                                                               "                   118                               140 H      2-CH.sub.3                                                                            4-CH.sub.3                                                                          Cl                                                                               "                   viscous mass                      141 H      2-CH.sub.3                                                                            5-CH.sub.3                                                                          Cl                                                                               "                   88                                142 H      2-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                                                     143 6-CH.sub.3                                                                            3-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                   114                               144 2-CH.sub.3                                                                            3-CH.sub.3                                                                            4-CH.sub.3 O                                                                        Cl                                                                               "                   oil                               145 H      2-CH.sub.3                                                                            4-Cl Cl                                                                               "                                                     146 H      2-CH.sub.3                                                                            5-Cl Cl                                                                               "                   122                               147 6-Cl   2-CH.sub.3                                                                            H    Cl                                                                               "                                                     148 H      3-Cl   H    Cl                                                                               "                   107                               149 H      3-Cl   4-Cl Cl                                                                               "                   146                               150 H      3-Cl   5-Cl Cl                                                                               "                   151                               151 6-Cl   2-Cl   H    Cl                                                                               "                                                     152 4-CH.sub.3 O                                                                          3-Cl   2-CH.sub.3                                                                          Cl                                                                               "                                                     153 H      2,3-(CH.sub.2 ).sub.3                                                                      Cl                                                                               "                                                     154 H      2,3-(CH.sub.2).sub.4                                                                       Cl                                                                               "                                                     155 6-CH.sub.3                                                                            2,3-(CH.sub.2).sub.3                                                                       Cl                                                                               "                                                     156 H      3,4-(CH.sub.2).sub.3                                                                       Cl                                                                               "                   124                               157 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR34##          158                               158 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   90-93                             159 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   122-24                            160 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR35##          131                               161 2-C.sub.2 H.sub.5                                                                     6-CH.sub.3                                                                            H    Cl                                                                               "                   85                                162 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   71-73                             163 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR36##                                            164 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     165 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR37##                                            166 2-C.sub.2 H.sub.5                                                                     6-CH.sub.3                                                                            H    Cl                                                                               "                                                     167 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR38##                                            168 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR39##                                            169 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR40##                                            170 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR41##                                            171 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR42##                                            172 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   103-104                           173 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     174 2-CH.sub.3                                                                            6-CH(CH.sub.3).sub.2                                                                  H    Cl                                                                               "                                                     175 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR43##                                            176 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR44##                                            177 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     178 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     179 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR45##                                            180 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR46##                                            181 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR47##          oil                               182 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR48##          162                               183 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR49##                                            184 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR50##          103-105                           185 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR51##          94                                186 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR52##                                            187 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR53##                                            188 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR54##                                            189 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   148                               190 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR55##                                            191 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR56##          145                               192 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR57##                                            193 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR58##                                            194 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR59##                                            195 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR60##          133-135                           196 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR61##                                            197 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR62##                                            198 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR63##          58                                199 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   67                                200 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR64##          118                               201 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   94                                202 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   94                                203 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR65##          108-112                           204 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR66##          127                               205 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   106                               206 2-CH.sub. 3                                                                           6-CH.sub.3                                                                            H    Cl                                                                                ##STR67##          116                               207 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR68##          95                                208 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   88                                209 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   104                               210 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                                ##STR69##          162                               211 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR70##          170                               212 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   165                               213 2-CH.sub.3                                                                            2-CH.sub.3                                                                            H    Cl                                                                                ##STR71##          114                               214 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   100                               215 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR72##          161                               216 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   112                               217 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR73##          168                               218 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                   170                               219 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                                ##STR74##          168                               220 H      H      H    Cl                                                                                ##STR75##                                            221 2-CH.sub.3                                                                            H      H    Cl                                                                                ##STR76##                                            222 H      H      H    Cl                                                                                ##STR77##                                            223 H      H      H    Cl                                                                                ##STR78##                                            224 2-CH.sub.3                                                                            6-CH.sub.3                                                                            H    Cl                                                                               "                                                     225 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                      226 2-C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     227 H      H      H    Cl                                                                                ##STR79##                                            228 2-CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                     H    Cl                                                                               "                                                     __________________________________________________________________________

The active ingredients according to the invention may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used; in any case they should ensure as fine a distribution of the active ingredient as possible.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, etc. and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenol polyglycol ethers, alkylaryl polyester alcohols, isotridecyl alcohols, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient.

The new herbicidal anilides according to the invention may be mixed and jointly applied with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable components are diazines, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, biscarbamates, thiocarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, etc. Such combinations broaden the spectrum of action and often achieve synergistic effects. A number of active ingredients which, together with the new compounds, give useful compositions for the most varied areas of application, are given below:

    ______________________________________                                          ##STR80##                                                                     R                R.sup.1       R.sup.2                                         ______________________________________                                          ##STR81##       NH.sub.2      Cl                                               ##STR82##       NH.sub.2      Br                                               ##STR83##       NH.sub.2      Cl                                               ##STR84##                                                                                       ##STR85##    Cl                                               ##STR86##       NHCH.sub.3    Cl                                               ##STR87##       NHCH.sub.3    Cl                                               ##STR88##                                                                                       ##STR89##    Cl                                              ______________________________________                                          ##STR90##                                                                     R            R.sup.1  R.sup.2                                                                                R.sup.3                                          ______________________________________                                         H            i-C.sub.3 H.sub.7                                                                       H      H     or salts of this                                                               compound                                    H            i-C.sub.3 H.sub.7                                                                       H      CH.sub.3                                                                             or salts of this                                                               compound                                    CH.sub.2OCH.sub.3                                                                           i-C.sub.3 H.sub.7                                                                       H      H                                                  ##STR91##               or salts of this compound                             ______________________________________                                          ##STR92##                                                                     R     R.sup.1   R.sup.2 R.sup.3     R.sup.4                                    ______________________________________                                         H     F.sub.3 C H       C.sub.2 H.sub.5                                                                            C.sub.4 H.sub.9                            H     F.sub.3 C H       n-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                          H     F.sub.3 C H       CH.sub.2CH.sub.2 Cl                                                                        n-C.sub.3 H.sub.7                          H     SO.sub.2 NH.sub.2                                                                        H       n-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                          H     F.sub.3 C H       n-C.sub.3 H.sub.7                                                                           ##STR93##                                 H.sub.3 C                                                                            H.sub.3 C H       H           CH(C.sub.2 H.sub.5).sub.2                  H     F.sub.3 C NH.sub.2                                                                               n-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                          H     H.sub.3 C H       n-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                          ______________________________________                                          ##STR94##                                                                     R           R.sup.1 R.sup.2                                                    ______________________________________                                          ##STR95##  H       i-C.sub.3 H.sub.7                                           ##STR96##  H       CH(CH.sub.3)CCH                                             ##STR97##  H       CH.sub.2CCCH.sub.2 Cl                                       ##STR98##  H       i-C.sub.3 H.sub.7                                           ##STR99##  H       CH(CH.sub.3)CONHC.sub.2 H.sub.5                             ##STR100## H       NC(CH.sub.3).sub.2                                         ______________________________________                                          ##STR101##                                                                    R                 R.sup.1     R.sup.2                                          ______________________________________                                          ##STR102##       H           CH.sub.3                                          ##STR103##       H           C.sub.2 H.sub.5                                   ##STR104##       CH.sub.3    CH.sub.3                                         ______________________________________                                          ##STR105##                                                                    R           R.sup.1     R.sup.2                                                ______________________________________                                         i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                                          CH.sub.2CClCCl.sub.2                                   i-C.sub.3 H.sub.7                                                                          i-C.sub.3 H.sub.7                                                                          CH.sub.2CClCHCl                                        n-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                                                          C.sub.2 H.sub.5                                         ##STR106## C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                        sec.-C.sub.4 H.sub.9                                                                       sec.-C.sub.4 H.sub.9                                                                       C.sub.2 H.sub.5                                        n-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                                                          n-C.sub.3 H.sub.7                                      i-C.sub.4 H.sub.9                                                                          i-C.sub.4 H.sub.9                                                                          C.sub.2 H.sub.5                                         ##STR107## C.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                        ______________________________________                                          ##STR108##                                                                    ______________________________________                                         CH.sub.2CClCHCl                                                                CH.sub.2CClCCl.sub.2                                                           ______________________________________                                          ##STR109##                                                                    R                 X     Y      R.sup.1                                         ______________________________________                                         CH.sub.3          Cl    Cl     Na                                               ##STR110##       Cl    H      CH.sub.3                                         ##STR111##       H     H      H, or salts of this compound                    Cl                Cl    Cl     Na                                               ##STR112##       H     CH.sub.3                                                                              CH.sub.3                                         ##STR113##       H     CH.sub.3                                                                              C.sub.2 H.sub.5                                 C.sub.2 H.sub.5   Cl    Cl     Na                                               ##STR114##       H     CH.sub.3                                                                              i-C.sub.3 H.sub.7                                ##STR115##       H     CH.sub.3                                                                              CH.sub.3                                         ##STR116##       H     CH.sub.3                                                                              CH.sub.2CH(CH.sub.3).sub.2                       ##STR117##       H     CH.sub.3                                                                              Na                                              ______________________________________                                          ##STR118##                                                                     R  R.sup.1   R.sup.2 R.sup.3          X                                       ______________________________________                                         H   tert.C.sub.4 H.sub.9                                                                     H       C.sub.2 H.sub.5  SCH.sub.3                               H   i-C.sub.3 H.sub.7                                                                        H       i-C.sub.3 H.sub.7                                                                               SCH.sub.3                               H   i-C.sub.3 H.sub.7                                                                        H       C.sub.2 H.sub.5  SCH.sub.3                               H   CH.sub.3  H       i-C.sub.3 H.sub.7                                                                               SCH.sub.3                               H   i-C.sub.3 H.sub.7                                                                        H       C.sub.2 H.sub.5  Cl                                      H   i-C.sub.3 H.sub.7                                                                        H                                                                                       ##STR119##      Cl                                      H   C.sub.2 H.sub.5                                                                          H       C.sub.2 H.sub.5  Cl                                      H   C.sub.2 H.sub.5                                                                          H                                                                                       ##STR120##      Cl                                      H   i-C.sub.3 H.sub.7                                                                        H       i-C.sub.3 H.sub.7                                                                               Cl                                      H   i-C.sub.3 H.sub.7                                                                        H       i-C.sub.3 H.sub.7                                                                               OCH.sub.3                                    ##STR121##                                                                              H                                                                                       ##STR122##      Cl                                      H   C.sub.2 H.sub.5                                                                          H       CH(CH.sub.3)CH.sub.2OCH.sub.3                                                                   Cl                                      H   C.sub.2 H.sub.5                                                                          H       CH(CH.sub.3)CCH  Cl                                      ______________________________________                                          ##STR123##                                                                    R                R.sup.1 R.sup.2                                               ______________________________________                                         CH.sub.3         CH.sub.3                                                                               CH(C.sub.6 H.sub.5).sub.2                              ##STR124##      H                                                                                       ##STR125##                                           C.sub.2 H.sub.5  C.sub.2 H.sub.5                                                                         ##STR126##                                           HCCC(CH.sub.3).sub.2                                                                            H                                                                                       ##STR127##                                            ##STR128##      H       CH.sub.3                                              ______________________________________                                          ##STR129##                                                                    R               R.sup.1 R.sup.2                                                                               R.sup.3                                         ______________________________________                                          ##STR130##     H       CH.sub.3                                                                              CH.sub.3                                         ##STR131##     H       CH.sub.3                                                                              H                                                ##STR132##     H       CH.sub.3                                                                              CH.sub.3                                         ##STR133##     H       CH.sub.3                                                                              CH.sub.3                                         ##STR134##     H       CH.sub.3                                                                              OCH.sub.3                                        ##STR135##     H       CH.sub.3                                                                              OCH.sub.3                                        ##STR136##     H       CH.sub.3                                                                              OCH.sub.3                                        ##STR137##     H       CH.sub.3                                                                              OCH.sub.3                                        ##STR138##     H       CH.sub.3                                                                              CH.sub.3                                         ##STR139##         H      CH.sub.2CH(CH.sub.3).sub.2                           ##STR140##     CH.sub.3                                                                               H      CH.sub.3                                        ______________________________________                                          ##STR141##                                                                    R      R.sup.1 R.sup.2                                                                               R.sup.3                                                  ______________________________________                                         NO.sub.2                                                                              CF.sub.3                                                                               H      H                                                        Cl     CF.sub.3                                                                               H      COOH,     or salts or esters of                                                          this compound                                  Cl     Cl      H                                                                                      ##STR142##                                              H      CF.sub.3                                                                               Cl     OC.sub.2 H.sub.5                                         ______________________________________                                          ##STR143##                                                                    R                 R.sup.1     R.sup.2                                          ______________________________________                                         tert.C.sub.4 H.sub.9                                                                             NH.sub.2    SCH.sub.3                                         ##STR144##       NH.sub.2    CH.sub.3                                         ______________________________________                                          ##STR145##                                                                    R          R.sup.1                                                                               R.sup.2      R.sup.3                                         ______________________________________                                         H          CH.sub.3                                                                              Br                                                                                           ##STR146##                                     H          CH.sub.3                                                                              Cl           tert.C.sub.4 H.sub.9                            H          CH.sub.3                                                                              Cl                                                                                           ##STR147##                                     H          (CH.sub.2).sub.3                                                                                ##STR148##                                         ______________________________________                                          ##STR149##                                                                    R               R.sup.1                                                        ______________________________________                                         CH.sub.3        C.sub.2 H.sub.5                                                 ##STR150##     C.sub.2 H.sub.5                                                 ##STR151##     C.sub.2 H.sub.5                                                 ##STR152##                                                                     ##STR153##                                                                     ##STR154##                                                                    ______________________________________                                          ##STR155##                                                                    R     R.sup.1       R.sup.2       R.sup.3                                      ______________________________________                                         H     n-C.sub.3 H.sub.7                                                                            CH.sub.2CHCH.sub.2                                                                           CH.sub.3                                     Na    n-C.sub.3 H.sub.7                                                                            CH.sub.2CHCH.sub.2                                                                           CH.sub.3                                      ##STR156##             or salts or esters of this compound                     ##STR157##                                                                     ##STR158##                                                                     ##STR159##                                                                     ##STR160##                                                                     ##STR161##          or salts, esters or amides of this compound                ##STR162##          or salts, esters or amides of this compound                ##STR163##          or salts, esters or amides of this compound                ##STR164##                                                                     ##STR165##                                                                     ##STR166##          or salts of this compound                                  ##STR167##                                                                     ##STR168##          or salts of this compound                                 ______________________________________                                    

It is also useful to apply the new compounds of the invention, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combatting pests, or phytopathogenic fungi or bacteria. Of further interest is the fact that the compounds may be mixed with mineral solutions used to eliminate nutritional and trace element deficiencies.

The influence of various representatives of the compounds of the invention on the growth of unwanted and crop plants, compared with prior art active ingredients which are chemically similar, is demonstrated in the following experiments. The series of experiments were carried out in the greenhouse and in the open.

I. Greenhouse experiments

The vessels employed were plastic flowerpots having a volume of 300 cm³ ; the substrate was a sandy loam containing about 1.5% humus. The seeds of the test plants (see Table 1) were sown shallow, and separated according to species. In the case of Cyperus esculentus, pregerminated tubers were planted. In the preemergence treatment, the active ingredients were then immediately applied to the surface of the soil. They were suspended or emulsified in water as the vehicle, and sprayed through atomizing nozzles. After the agents had been applied, the vessels were lightly sprinkler-irrigated to set germination and growth going, and to activate the chemical agents. The vessels were then covered with transparent plastic hoods until the plants had taken root. This cover ensured uniform germination of the test plants (to the extent that this was not impaired by the chemicals), and prevented readily volatile substances from evaporating.

For postemergence treatment, the plants were first grown to a height of from 3 to 10 cm, depending on their habit, before before treated. Hoods were not placed on the pots. The experiments were set up in the greenhouse, hotter areas (25° to 40° C.) being preferred for heat-loving species, and 15° to 30° C. for plants from moderate climates. The experiments were carried out for from 4 to 6 weeks. During this period the plants were tended and their reaction to the various treatments was assessed. The following tables contain the substances investigated, the application rates in kg/ha of active ingredient, and the test plant species. Assessments were made on a 0 to 100 scale, 0 denoting no damage or normal emergence, and 100 denoting no emergence or complete destruction of at least the visible plant parts.

II. Experiments in the open

The experiments were carried out on small plots. The soil was a sandy loam having a pH of from 5 to 6 and containing from 1 to 1.5% humus. The treatment was preemergence, the active ingredients being applied immediately or at the latest 3 days after sowing. The crop plants were sown in rows. The weed flora was made up of the most widely varying species and was natural; the weed flora depended on the time of the year and in part on the crop (e.g., spring-germinating, summer-germinating). The substances were emulsified or suspended in water as the vehicle, and applied by means of a motor-driven plot spray mounted on a hitch. When no rain fell, the plots were watered to ensure germination and growth of the crop plants and weeds. All the experiments were run for several weeks. Over this period, assessments were made at certain intervals on the 0 to 100 scale.

Results

Tables 2 to 15 contain the results.

It was astounding what a comprehensive and vehement herbicidal effect some of the anilides of the invention had on unwanted plants even at the lowest application rates (Tables 2, 10). What was also surprising was the stronger action of the new compounds on unwanted broadleaved species. In this area, too, the new active ingredients had a clear advantage over prior art compounds (Tables 3, 4, 5, 9, 10).

For crop plants there were sufficient safety margins between herbicidal action on the one hand and tolerance on the other to justify the use of the new compounds as selective herbicides (Tables 3, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15).

In postemergence treatment, complete withering of the plants was possible, depending on the application rate (Table 4). When sublethal doses were given, however, growth inhibition resulted which would seem to be of interest in areas in which merely a growth-regulating action on unwanted plants is desired without their being destroyed, e.g., verges, reafforestation areas and lawns.

The herbicidal action of the new compounds is sufficiently intensive to completely destroy all herbaceous plant growth with application rates in excess of those used for selective control. Possible application areas here are the removal of unwanted plants in bush and tree crops, and in industrial plants, along railroad tracks, and on squares, playgrounds, etc.

In the tables, the application is given as pre- or postemergence. It is of course also possible for the agents to be incorporated into the soil in addition to the surface application. The agents may be incorporated before sowing, after sowing or between already established crop plants.

Another application method is post-directed or lay-by spraying. In this method, the spray is directed past the leaves of the sensitive crop plants onto the surface of the soil or the unwanted plants.

In view of the numerous application methods possible, the agents according to the invention, or compositions containing them, may be used in a large number of crop plants, in addition to those listed in the tables, for removing or inhibiting unwanted plants. The application rates may vary from 0.1 to 15 kg/ha and more, depending on the purpose for which they are used. The crop plants employed in the experiments are listed below:

                  TABLE 1                                                          ______________________________________                                         Botanical name      Common name                                                ______________________________________                                         Allium cepa         onion                                                      Ananas comosus      pineapple                                                  Arachis hypogaea    peanut (groundnut)                                         Asparagus officinalis                                                                              asparagus                                                  Avena sativa        oats                                                       Beta vulgaris spp. altissima                                                                       sugarbeet                                                  Beta vulgaris spp. rapa                                                                            fodder beet                                                Beta vulgaris spp. esculenta                                                                       table beet, red beet                                       Brassica napus var. napus                                                                          rape                                                       Brassica napus var. napobrassica                                               Brassica napus var. napa                                                                           turnip                                                     Brassica rapa var. silvestris                                                  Camellia sinensis   tea plant                                                  Carthamus tincotius safflower                                                  Citrus limon        lemon                                                      Citrus maxima       grapefruit                                                 Citrus reticulata                                                              Citrus sinensis     orange                                                     Coffea arabica (Coffea canephora,                                                                  coffee                                                     Coffea liberica)                                                               Cucumis melo        melon                                                      Cucumis sativus     cucumber                                                   Cynodon dactylon    Bermudagrass in turf                                                           and lawns                                                  Daucus carota       carrot                                                     Elaesis guineensis  oil palm                                                   Fragaria vesca      strawberry                                                 Glycine max         soybean                                                    Gosspyium hirsutum  cotton                                                     (Gossypium arboreum                                                            Gossypium herbaceum                                                            Gossypium vitifolium)                                                          Helianthus annuus   sunflower                                                  Helianthus tuberosus                                                           Hevea brasiliensis  rubber plant                                               Hordeum vulgare     barley                                                     Humulus lupulus     hops                                                       Ipomoea batatas     sweet potato                                               Lactuca sativa      lettuce                                                    Lens culinaris      lentil                                                     Linum usitatissimum flax                                                       Lycopersicon lycopersicum                                                                          tomato                                                     Malus spp.          apple                                                      Manihot esculenta   cassava                                                    Medicago sativa     alfalfa (lucerne)                                          Mentha piperita     peppermint                                                 Musa spp.           banana                                                     Nicotiana tabacum   tobacco                                                    (N. rustica)                                                                   Olea europaea       olive                                                      Oryza sativa        rice                                                       Panicum miliaceum                                                              Phaseolus lunatus   limabean                                                   Phaseolus mungo     mungbean                                                   Phaseolus vulgaris  snapbean, green bean,                                                          dry bean                                                   Pennisetum glaucum                                                             Petroselinum crispum                                                                               parsley                                                    spp. tuberosum                                                                 Picea abies         Norway spruce                                              Abies alba          fir                                                        Pinus spp.          pine                                                       Pisum sativum       English pea                                                Prunus avium        cherry                                                     Prunus domestica    plum                                                       Prunus persica      peach                                                      Pyrus communis      pear                                                       Ribes sylvestre     redcurrant                                                 Ribes uva-crispa                                                               Ricinus communis                                                               Saccharum officinarum                                                                              sugar cane                                                 Secale cereale      rye                                                        Sesamum indicum     Sesame                                                     Solanum tuberosum   Irish potato                                               Sorghum bicolor (s. vulgare)                                                                       grain sorghum                                              Sorghum dochna                                                                 Spinacia oleracea   spinach                                                    Theobroma cacao     cacao                                                      Trifolium pratense  red clover                                                 Triticum aestivum   wheat                                                      Vaccinium corymbosum                                                                               blueberry                                                  Vaccinium vitis-idaea                                                                              cranberry                                                  Vicia faba          tick bean                                                  Vigna sinensis (V. unguiculata)                                                                    cow pea                                                    Vitis vinifera      grape                                                      Zea mays            Indian corn, sweet corn,                                                       maize                                                      ______________________________________                                    

                                      TABLE 2                                      __________________________________________________________________________     Intensity of action of haloacetanilides on certain                             plants; preemergence treatment in the greenhouse                                ##STR169##                                                                                             Appl.                                                                              Test plants and % damage                          Compound                                                                              Substituents      rate                                                                               Amar.                                                                              Bromus                                                                              Cyp.                                                                               Chrys.                                                                             Euph.                                                                              Poa  Solanum                                                                            Sorgh.              No.    R   R.sup.1                                                                            A         kg/ha                                                                               retro.                                                                            spp. diff.                                                                              seget.                                                                             gen.                                                                               annua                                                                               nigrum                                                                             halep.              __________________________________________________________________________     prior  C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                    OCH.sub.3 0.125                                                                              --   50   65 --  --   80  --  40                  art                      0.25                                                                                72  80   70  30  60  98   50 38                  prior art                                                                             CH.sub.3                                                                           CH.sub.3                                                                            ##STR170##                                                                              0.25 0.5                                                                            75  88  90                                                                              65 --  0                                                                              --  25                                                                              0  15                                                                              --  80                                                                             50 50                5     CH.sub.3                                                                           CH.sub.3                                                                            ##STR171##                                                                              0.125 0.25                                                                         100  90  95                                                                             100 100                                                                            -- 100                                                                             -- 100                                                                             100 100                                                                             -- 100                                                                             95 95               67     CH.sub.3                                                                           CH.sub.3                                                                            ##STR172##                                                                              0.25                                                                               100 100  --  --  --  --   --  95                  38     CH.sub.3                                                                           CH.sub.3                                                                            ##STR173##                                                                              0.125 0.25                                                                          75 100                                                                             95 100                                                                             100 100                                                                            -- --                                                                              -- --                                                                              100 100                                                                             -- --                                                                              70 95                7     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     ##STR174##                                                                              0.125 0.25                                                                         --  88                                                                             --  95                                                                              -- --                                                                              -- 100                                                                             --  80                                                                             -- 100                                                                              -- 100                                                                             -- 75               40     CH.sub.3                                                                           C.sub.2 H.sub.5                                                                     ##STR175##                                                                              0.125 0.25                                                                          90 100                                                                            --  80                                                                              100 100                                                                            --  30                                                                             --  0                                                                              -- 100                                                                               95 60 60                8     C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                     ##STR176##                                                                              0.25                                                                                95 100  --  --  --  --   --  85                  70     C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5                                                                     ##STR177##                                                                              0.25                                                                               100 100  --  --  --  --   --  75                  __________________________________________________________________________      0 = no damage                                                                  100 = complete destruction                                               

                                      TABLE 3                                      __________________________________________________________________________     Removal of unwanted plants in rape with haloacetanilides;                      preemergence application in the open                                            ##STR178##                                                                                           Appl.                                                                              Test plants and % damage                            Compound                                                                             Substituents     rate                                                                                Brassica                                                                           Alopec.                                                                             Anth./                                                                             Lamium                                                                              Stellaria                        No.   R  R.sup.1                                                                           A          kg/ha                                                                               napus                                                                              myosur.                                                                             Matric.                                                                            spp. media                            __________________________________________________________________________      5    CH.sub.3                                                                          CH.sub.3                                                                           ##STR179##                                                                               2.0  7.5 95   100 100  100                               40   CH.sub.3                                                                          C.sub.2 H.sub.5                                                                    ##STR180##                                                                               1.0 20   50    90  60   68                               38   CH.sub.3                                                                          CH.sub.3                                                                           ##STR181##                                                                               2.0  0   80   100 100   88                               7    CH.sub.3                                                                          C.sub.2 H.sub.5                                                                    ##STR182##                                                                               0.5 1.0                                                                             5 10                                                                               70 85                                                                               100 --                                                                              95 100                                                                              80  95                          129   CH.sub.3                                                                          C.sub.2 H.sub.5                                                                    ##STR183##                                                                               2.0 4.0                                                                             7.5 22.5                                                                           35 68                                                                                35  45  90                                                                              24  49                          191   CH.sub.3                                                                          C.sub.2 H.sub.5                                                                    ##STR184##                                                                               2.0 4.0                                                                             5 20                                                                               30 80                                                                                53 --                                                                              40  85                                                                              18  45                          prior C.sub.2 H.sub. 5                                                                  C.sub.2 H.sub.5                                                                   OCH.sub.3  2.0  5   65    53 --    15                              art                                                                            __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 4                                      __________________________________________________________________________     Herbicidal action of haloacetanilides;                                         postemergence application in the greenhouse                                     ##STR185##                                                                                          Appl.                                                                              Test plants and % damage                             Compound                                                                             Substituents    rate                                                                                Alopec.                                                                            Avena                                                                              Cyper.                                                                             Chrys.                                                                             Matric.                                                                            Setaria                                                                            Stell.                      No.   R  R.sup.1                                                                           A         kg/ha                                                                               myosur.                                                                            fat.                                                                               escul.                                                                             seget.                                                                             spp.                                                                               spp.                                                                               med.                        __________________________________________________________________________     prior C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                   OCH.sub.3 1.0 60   50  42  15  50  68   0                          art                   2.0 60   70  55  15  50  68   30                          5    CH.sub.3                                                                          CH.sub.3                                                                           ##STR186##                                                                              1.0 2.0                                                                            80 90                                                                               90 92                                                                              70 72                                                                              98 98                                                                              95 95                                                                              82 85                                                                                95  98                     38   CH.sub.3                                                                          CH.sub.3                                                                           ##STR187##                                                                              1.0 2.0                                                                            -- --                                                                               70 90                                                                              80 80                                                                              -- --                                                                              -- --                                                                              85 85                                                                              100 100                      68   C.sub.2 H.sub.5                                                                   CH.sub.3                                                                           ##STR188##                                                                              1.0 2.0                                                                            90 90                                                                               90 90                                                                              85 85                                                                              40 50                                                                              80 80                                                                              90 95                                                                               60  60                     189   C.sub.2 H.sub.5                                                                   CH.sub.3                                                                           ##STR189##                                                                              1.0 2.0                                                                            70 70                                                                               60 60                                                                              65 65                                                                               0 20                                                                              30 60                                                                              80 85                                                                               0  40                      158   C.sub.2 H.sub.5                                                                   CH.sub. 3                                                                          ##STR190##                                                                              1.0 2.0                                                                            70 90                                                                               75 75                                                                              50 65                                                                              20 40                                                                              50 95                                                                              85 85                                                                               0  40                      __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 5                                      __________________________________________________________________________     Herbicidal action and crop plant tolerance of haloacetanilides;                preemergence application in the open                                            ##STR191##                                                                                       Appl.                                                                              Test plants and % damage                                Compound                                                                             Substituents rate                                                                                Glyc.                                                                             Amar.                                                                              Chenop.                                                                             Echin.                                                                             Galins.                                No.   R  R.sup.1                                                                           A      kg/ha                                                                               max                                                                               retro.                                                                             spp. c.g.                                                                               spp.                                   __________________________________________________________________________     5     CH.sub.3                                                                          CH.sub.3                                                                           ##STR192##                                                                           0,5 1,0                                                                            0 4 100 100                                                                            69 85                                                                               100 100                                                                            91 100                                 prior C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                   OCH.sub.3                                                                             0,1 0   --  10   65  30                                     art                1,0 0   80  13   73  55                                     __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 6                                      __________________________________________________________________________     Tolerance of some haloacetanilides by soybeans and                             cotton, combined with good herbicidal action;                                  preemergence application in the greenhouse                                      ##STR193##                                                                                             Appl.                                                                              Test plants and % damage                          Compound                                                                             Substituents       rate                                                                                Glyc.                                                                             Gossyp.                                                                            Amar.                                                                              Cyper.                                                                             Echin.                                                                             Euph.                                                                               Setaria                                                                            Solanum              No.   R  R.sup.1                                                                           A            kg/ha                                                                               max                                                                               hirs.                                                                              retro.                                                                             escul.                                                                             c.g.                                                                               genic.                                                                              spp.                                                                               nigrum               __________________________________________________________________________     prior C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                   OCH.sub.3    0,5 0   0   100 40  65  20   60  95                   art                      1,0 0   20  100 50  90  45   90  100                                           2,0 0   40  100 60  95  100  100 100                   68   C.sub.2 H.sub.5                                                                   CH.sub.3                                                                           ##STR194##  0,25 1,0 2,0                                                                       0 0 10                                                                             0 5 5                                                                              95 100 100                                                                         65 80 80                                                                           95 95 95                                                                           10 60 75                                                                            95 100 100                                                                         95 100 100           189   C.sub.2 H.sub.5                                                                   CH.sub.3                                                                           ##STR195##  0,5 1,0 2,0                                                                        0 0 0                                                                              0 20 20                                                                            30 95 95                                                                           50 60 80                                                                           90 95 95                                                                           90 95 95                                                                            75 95 100                                                                          30 95 95             158   C.sub.2 H.sub.5                                                                   CH.sub.3                                                                           ##STR196##  0,5 1,0 2,0                                                                        0 10 20                                                                            0 0 95 100 100                                                                         55 75 75                                                                           95 95 95                                                                           60 90 90                                                                            90 95 100                                                                          95 100 100           130   C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                    ##STR197##  0,5 1,0 2,0                                                                        20 20 20                                                                           20 30 30                                                                           95 100 100                                                                         40 70 80                                                                           95 100 100                                                                         60 60 100                                                                           85 95 100                                                                          100 100 100          159   C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                    ##STR198##  0,5 1,0 2,0                                                                        0 0 0                                                                              0 10 20                                                                            85 95 100                                                                          40 65 70                                                                           80 95 100                                                                          20 50 55                                                                            75 90  100                                                                         50 95 95             __________________________________________________________________________      0 = no damage                                                                  100 = plants withered                                                    

                                      TABLE 7                                      __________________________________________________________________________     Selective herbicidal action of haloacetanilides;                               preemergence application in the greenhouse                                      ##STR199##                                                                                    Appl.                                                                              Test plants and % damage                                   Compound                                                                             Substituent                                                                              rate                                                                                Glyc.                                                                             Gossyp.                                                                            Amar.                                                                              Cenchr.                                                                             Cyp.                                                                              Echin.                                                                             Ipom.                                                                              Lept.                                                                             Panic.                                                                             Sida                                                                              Solan.               No.   A         kg/ha                                                                              max hirs.                                                                              retro.                                                                             ech. diff.                                                                             c.g.                                                                               spp.                                                                               spp.                                                                              virg.                                                                              spin.                                                                             nigr.                __________________________________________________________________________     41                                                                                    ##STR200##                                                                              0,25 0,5 1,0 2,0                                                                   0 0 0 0                                                                            0 8 8 10                                                                           73 97  100 100                                                                     90 92 100 100                                                                       100 100 100 --                                                                    95 100 100 100                                                                     -- -- 50 90                                                                        95 95 95 95                                                                       85 85 100 100                                                                      -- -- 45 90                                                                       70 90 98 100         bekannt                                                                              OCH.sub.3 0,25                                                                               0   0   68  92   65 45  --  100                                                                               30  -- 50                                   0,5 0   6   81  95   70 75  --  100                                                                               45  -- 73                                   1,0 0   20  88  100  78 90  20  100                                                                               92  10 90                                   2,0 0   45  92  100  100                                                                               95  30  100                                                                               100 70 90                   __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 8                                      __________________________________________________________________________     Tolerance of a further herbicidal haloacetanilide by various oil crops         in the greenhouse                                                                                           Test plants and % damage                          Compound               Appl. rate                                                                           Brassica                                                                            Glyc..sup.x                                                                         Arach.                                                                            Carth.                                                                             Amar.                                                                              Seta.                                                                             Solan.                    no.   Structure        kg/ha napus                                                                               max hypog.                                                                             tinct.                                                                             retro.                                                                             spp.                                                                              nigrum.                   __________________________________________________________________________     127                                                                                   ##STR201##      0,5 1,0 2,0                                                                          0 0 0                                                                               0 0 0                                                                              0 0 10                                                                             0 0 --                                                                             82 95 100                                                                          95 100 100                                                                        70 90 100                 __________________________________________________________________________      0 =0 no damage                                                                 100 = no emergence or plants withered                                          .sup.x varieties: Dare, Lee 68, SRF 450                                  

                                      TABLE 9                                      __________________________________________________________________________     Tolerance and herbicidal action of haloacetanilides in various crops;          preemergence application in the greenhouse                                     Basic molecule                                                                  ##STR202##                                                                                                    Test plants and % damage                                                       Glyc.                                                                              Sorgh.                                                                              Zea                                                                               Amar.                                                                              Bromus                                                                              Echin.                    Compound No.                                                                           Substituent B  Appl. rate kg/ha                                                                         max                                                                               bic. mays                                                                              retro.                                                                             spp. c.g.                                                                               Setar.                __________________________________________________________________________                                                              spp.                  prior art                                                                              C.sub.3 H.sub.7 i                                                                             1.0      10   0   0   42 50   45   95                                          2.0      40   0   0   50 70   90  100                   34                                                                                      ##STR203##    1.0 2.0   0 0                                                                                0 10                                                                               0 0                                                                               100 100                                                                            95 95                                                                               90 90                                                                               80 95                __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 10                                     __________________________________________________________________________     Herbicidal action of selective haloacetanilides; preemergence application      in the greenhouse                                                              Basic molecule                                                                  ##STR204##                                                                                                Test plants and % damage                                                             Alo-                                         Com-                    Appl.  Gos-                                                                              pec.      Ech-   Ma-                                                                               Set-                                                                              Sorg.                 pound                                                                              Substituents        rate                                                                               Glyc.                                                                             syp.                                                                              myo-                                                                              Amar.                                                                              Cyp.                                                                              in.                                                                               Euph.                                                                              tric.                                                                             aria                                                                              ha-                                                                               Stell.             no. R  R.sup.1                                                                           R.sup.2                                                                           A          kg/ha                                                                               max                                                                              hirs.                                                                             sur.                                                                              retro.                                                                             diff.                                                                             c.g.                                                                              gen.                                                                               spp.                                                                              spp.                                                                              lep.                                                                              med.               __________________________________________________________________________     prior art                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H                                                                                  ##STR205##                                                                               0.25 0.5 1.0                                                                       10 20 25                                                                           0 0 10                                                                            40 80 80                                                                          80 80 100                                                                         100 100 100                                                                        95 100 100                                                                       15 30 50                                                                            50 80 90                                                                          70 90 100                                                                         30 40 70                                                                          20 70 70           14 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           ##STR206##                                                                               0.25 0.5 1.0                                                                       10 10 20                                                                           0 0 15                                                                            95 100 100                                                                       100 100 100                                                                        100 100 100                                                                       100 100 100                                                                       80 95 95                                                                            80 100 100                                                                       100 100 100                                                                         95 95 100                                                                        90 100 100         47 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           ##STR207##                                                                               0.25 0.5 1.0                                                                       20 20 30                                                                           0 0 0                                                                             95 100 100                                                                       100 100 100                                                                        100 100 100                                                                        95 95 100                                                                        10 10 20                                                                            80 90 100                                                                        100 100 100                                                                        85 90 95                                                                          30 80 100         136 CH.sub.3                                                                          CH.sub.3                                                                          CH.sub.3                                                                           ##STR208##                                                                               0.25 0.5 1.0                                                                       -- -- 10 10                                                                           -- 50 90                                                                          -- 70 70                                                                           -- 90 90                                                                          --  95 95                                                                        -- 45 65                                                                            -- 50 90                                                                          -- 90 100                                                                         -- 80 80                                                                          -- 30             __________________________________________________________________________                                                                 80                  0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 11                                     __________________________________________________________________________     Herbicidal action of further haloacetanilides; preemergence application        in the greenhouse                                                              Basic molecule                                                                  ##STR209##                                                                                                       Appl.                                                                              Test plants and % damage                Compound                                                                             Substituents                 rate                                                                                Alopec.                                                                            Amar.                                                                              Cyper.                                                                             Echin.                                                                             Set.                                                                              Sorgh.              No.   R.sup.1                                                                            R.sup.2                                                                           R.sup.3                                                                           R.sup.4                                                                           R   A           kg/ha                                                                               myosur.                                                                            retro.                                                                             diff.                                                                              c.g.                                                                               spp.                                                                              hale.               __________________________________________________________________________     162   C.sub.2 H.sub.5                                                                    H  H  H  C.sub.2 H.sub.5                                                                     ##STR210## 2.0  95  100 100 100 100                                                                               95                  4     H   H  H  H  i-C.sub.3 H.sub.7                                                                   ##STR211## 2.0  95   95  90 100  90                                                                               65                  17    CH.sub.3                                                                           CH.sub.3                                                                          H  H  H                                                                                   ##STR212## 2.0  50   90 100 100  90                                                                               75                  9     i-C.sub.3 H.sub.7                                                                  H  H  H  CH.sub.3                                                                            ##STR213## 2.0 100  100 100 100 100                                                                               90                  11    i-C.sub.3 H.sub.7                                                                  H  H  H  i-C.sub.3 H.sub.7                                                                   ##STR214## 2.0  90   90 100 100  80                                                                               70                  13    CH.sub.3                                                                           H  CH.sub.3                                                                          H  CH.sub.3                                                                            ##STR215## 2.0  80  100  90 100  90                                                                               80                  108   C.sub.2 H.sub.5                                                                    H  H  H  C.sub.2 H.sub.5                                                                     ##STR216## 2.0  70  100 100 100  90                                                                               60                  139   CH.sub.3                                                                           CH.sub.3                                                                          H  H  H                                                                                   ##STR217## 2.0  70   40  90  90  30                                                                               50                  36    H   H  H  H  C.sub.2 H.sub.5                                                                     ##STR218## 0.5 1.0                                                                             90 100                                                                              95 95                                                                              -- --                                                                              80 95                                                                              90 95                                                                            40 40               131   i-C.sub.3 H.sub.7                                                                  H  H  H  CH.sub.3                                                                            ##STR219## 2.0  70   80 100 100 100                                                                               80                  37    H   H  H  H  i-C.sub.3 H.sub.7                                                                   ##STR220## 1.0  30  100 100 100 100                                                                               80                  50    CH.sub.3                                                                           CH.sub.3                                                                          H  H  H                                                                                   ##STR221## 1.0  90  100 100 100 100                                                                               70                  52    CH.sub.3                                                                           H  H  CH.sub.3                                                                          H                                                                                   ##STR222## 2.0  60  100 100  95  90                                                                               60                  42    i-C.sub.3 H.sub.7                                                                  H  H  H  CH.sub.3                                                                            ##STR223## 1.0  95  100 100 100 100                                                                               90                  44    i-C.sub.3 H.sub.7                                                                  H  H  H  i-C.sub.3 H.sub.7                                                                   ##STR224## 2.0  80   80 100  90  90                                                                               40                  46    CH.sub.3                                                                           H  CH.sub.3                                                                          H  CH.sub.3                                                                            ##STR225## 1.0  60   90 100 100 100                                                                               80                  __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 12                                     __________________________________________________________________________     Herbicidal acetanilides selective in sugarbeet and                             other crops; preemergence application in the                                   greenhouse                                                                      ##STR226##                                                                                                    Test plants and % damage                       Compound                                                                             Substituents        Appl. rate                                                                           Beta                                                                              Glyc.                                                                             Sorgh.                                                                             Zea                                                                               Alopec.                                                                             Amar.                                                                              Setaria                  no.   R   R.sup.1                                                                           R.sup.2                                                                          A          ka/ha vulg.                                                                             max                                                                               bicol.                                                                             mays                                                                              myosur.                                                                             retro.                                                                             spp.                     __________________________________________________________________________     107   CH.sub.3                                                                           C.sub.2 H.sub.5                                                                   H                                                                                 ##STR227##  2.0 0  0  85  0  95   95  95                       106   CH.sub.3                                                                           CH.sub.3                                                                          H                                                                                 ##STR228##  1.0 2.0                                                                            10 10                                                                             10 10                                                                             70 70                                                                              15 50                                                                             100 100                                                                             95 95                                                                              90 95                    72    i-C.sub.3 H.sub.7                                                                  H  H                                                                                 ##STR229##  1.0 2.0                                                                            10 10                                                                             10 20                                                                             20 40                                                                              0 10                                                                              100 100                                                                             95 95                                                                              90 95                    69    C.sub.2 H.sub.5                                                                    H  H                                                                                 ##STR230##  0.5 20 20 10  0  100  95  80                       24    CH.sub.3                                                                           H  Cl                                                                                ##STR231##  2.0 60 10 10  0  100  95  85                       __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 13                                     __________________________________________________________________________      ##STR232##                                                                                  Appl.                                                            Substituents  rate                                                                               Test plants and % damage                                     R  R.sup.1                                                                           A       ka/ha                                                                               Beta vulg.                                                                         Alopec. myosur.                                                                        Echin c.g.                                                                          Setar. spp.                                __________________________________________________________________________     CH.sub.3                                                                          CH.sub.3                                                                           ##STR233##                                                                            1.0   0     20    40    20                                       CH.sub.3                                                                          CH.sub.3                                                                           ##STR234##                                                                            0.5 1.0                                                                              0 0   80 80 100 100                                                                              100 100                                  CH.sub.3                                                                          C.sub.2 H.sub.5                                                                    ##STR235##                                                                            0.5 1.0                                                                              0  0  100 100                                                                              100 100                                                                              100 100                                  __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 14                                     __________________________________________________________________________     Tolerance by various crop plants; preemergence application in the              greenhouse                                                                      ##STR236##                                                                                    Appl.                                                                              Test plants and % damage                                   Substituents    rate                                                                                Beta                                                                             Glyc.                                                                             Alopec.                                                                             Bromus                                                                              Cyperus                                                                             Echin.                                                                             Matric.                                                                            Setaria                       R  R.sup.1                                                                           A         kg/ha                                                                               vulg.                                                                            max                                                                               myosur.                                                                             spp. ferax                                                                               c.g.                                                                               spp.                                                                               spp.                          __________________________________________________________________________     CH.sub.3                                                                          CH.sub.3                                                                           ##STR237##                                                                              0.5 1.0                                                                            -- --                                                                             0 0                                                                               100 100                                                                             100 100                                                                             100 100                                                                             100 100                                                                            95 95                                                                              100 100                       CH.sub.3                                                                          C.sub.2 H.sub.5                                                                    ##STR238##                                                                              0.5 1.0                                                                            5 15                                                                              0 0                                                                               100 100                                                                             90 98                                                                               100 100                                                                             100 100                                                                            98 98                                                                              100 100                       C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                                                    ##STR239##                                                                              1.0 2.0                                                                            10 15                                                                             0 0                                                                               99 99                                                                               98 98                                                                               100 100                                                                             100 100                                                                            90 98                                                                              100 100                       CH.sub.3                                                                          CH.sub.3                                                                           ##STR240##                                                                              0.5 1.0                                                                            0 0                                                                               0 10                                                                              90 95                                                                               95 95                                                                               -- --                                                                               98 98                                                                              100 100                                                                            92 100                        CH.sub.3                                                                          CH.sub.3                                                                           ##STR241##                                                                              1.0 2.0                                                                            3 13                                                                              5 20                                                                              95 100                                                                              92 95                                                                               -- --                                                                               100 100                                                                            75 80                                                                              95 100                        CH.sub.3                                                                          C.sub.2 H.sub.5                                                                    ##STR242##                                                                              1.0 0  -- 90   90   --   100 60  85                            CH.sub.3                                                                          C.sub.2 H.sub.5                                                                    ##STR243##                                                                              3.0 -- -- --   --   --   100 --  --                            __________________________________________________________________________      0 = no damage                                                                  100 = no emergence or plants withered                                    

                                      TABLE 15                                     __________________________________________________________________________     Preemergence application in the greenhouse                                      ##STR244##                                                                                        Test plants and % damage                                   Substituents        Arach.                                                                             Brassica                                                                            Zea Alopec.                                                                             Bromus                                                                              Cyp.                                                                               Echin.                                                                             Matric.                                                                            Setar.                                                                             Solan.              R  R.sup.1                                                                           A         kg/ha                                                                               hypog.                                                                            napus                                                                               mays                                                                               myosur.                                                                             spp. diff.                                                                              c.g.                                                                               spp.                                                                               spp.                                                                               nigr.               __________________________________________________________________________     CH.sub.3                                                                          CH.sub.3                                                                           ##STR245##                                                                              0.5 0    5   20  95   95   100 90  95  98   85                 H  CH.sub.3                                                                           ##STR246##                                                                              1.0 --  10    0  85   95   --  85  90  60  100                 H  CH.sub.3                                                                           ##STR247##                                                                              2.0 --   0   15  90   80   --  95  90  95   95                 H  CH.sub.3                                                                           ##STR248##                                                                              2.0 --  10    0  90   90   --  95  90  100 100                 H  CH.sub.3                                                                           ##STR249##                                                                              2.0 --  30   10  50   80   --  55  95  100 100                 CH.sub.3                                                                          CH.sub.3                                                                           ##STR250##                                                                              1.0 0    5   --  97   98   100 100 92  100 100                 CH.sub.3                                                                          CH.sub.3                                                                           ##STR251##                                                                              2.0 15  --   15  98   98   --  100 100 95  --                  __________________________________________________________________________ 

We claim:
 1. An acetanilide of the formula ##STR252## where R is hydrogen, alkyl of a maximum of 5 carbon atoms, or alkoxy of a maximum of 5 carbon atoms, R' is hydrogen, halogen, alkyl of a maximum of 5 carbon atoms, alkoxy of a maximum of 5 carbon atoms, perhaloalkyl of a maximum of 4 carbon atoms, or alkoxyalkyl of a maximum of 5 carbon atoms, R² is hydrogen, halogen, alkyl of a maximum of 5 carbon atoms, alkoxy of a maximum of 5 carbon atoms, perhaloalkyl of a maximum of 4 carbon atoms, or alkoxyalkyl of a maximum of 5 carbon atoms, X is chloro, bromo, or iodo, and A is azole selected from the group consisting of 1,2,4-triazole and 1,2,3-triazole which is linked via a ring nitrogen atom and is unsubstituted or mono- or polysubstituted by halogen, phenyl, alkyl, alkoxy, alkylthio or perfluoroalkyl, each of maximum of 4 carbon atoms, or A is an acid addition salt of the azole cyano, carboxy, carbalkoxy of a maximum of 4 carbon atoms in the alkoxy group, or alkanoyl of a maximum of 4 carbon atoms.
 2. An acetanilide of the formula ##STR253## where R is hydrogen, alkyl of a maximum of 5 carbon atoms, or alkoxy of a maximum of 5 carbon atoms, R' is hydrogen, halogen, alkyl of a maximum of 5 carbon atoms, alkoxy of a maximum of 5 carbon atoms, perhaloalkyl of a maximum of 4 carbon atoms, or alkoxyalkyl of a maximum of 5 carbon atoms, R² is hydrogen, halogen, alkyl of a maximum of 5 carbon atoms, alkoxy of a maximum of 5 carbon atoms, perhaloalkyl of a maximum of 4 carbon atoms, or alkoxyalkyl of a maximum of 5 carbon atoms, X is chloro, bromo, or iodo, and A is a C₁ -C₄ alkoxy substituted pyrazole which is linked via a ring nitrogen atom, or A is an acid addition salt of the C₁ -C₄ alkoxy substituted pyrazole.
 3. An acetanilide of the formula I as defined in claim 1, wherein A is a 1,2,3-triazole group.
 4. An acetanilide of the formula I as defined in claim 1, wherein A is a 1,2,4-triazole group.
 5. An acetanilide as defined in claim 2, wherein the alkoxy is methoxy.
 6. An acetanilide as defined in claim 5, wherein X is chloro.
 7. 2-Chloro-2',3',6'-trimethyl-N-(pyrazol-1-yl-methyl)acetanilide.
 8. 2-chloro-2',6'-dimethyl-N-(3,5-dimethylpyrazol-1-yl-methyl)acetanilide.
 9. 2-chloro-2'-6'-dimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide.
 10. 2-chloro-2',3',6'-trimethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide.
 11. 2-chloro-2',6'-diethyl-N-(1,2,4-triazol-1-yl-methyl)-acetanilide.
 12. 2-chloro-2',6'-dimethyl-N-(3(5)-methyl-1,2,4-triazol-1-yl-methyl)-acetanilide. 